PROCESS OF PRODUCING ω-ARA-ALKYLOXYPHENYLETHYLAMINS AND THEIR N-ALKYL DERIVATIVES.



-' i o GUSTAV REINIGKE, OF SCHONEIBERG, NEAR BERLIN, GERMANY ASSIGNOR 'I'O ACTIEN GESELLSCHAFT ANILIN FABRIKATION, OF BERLIN, GERMANY.

rnoonss or PRODUCING w-PARA-ALKYLOXYPHENYLETHYLAMIN S AND'THEIR 'N- LKYL DERIVATIVES.

No Drawing.

To all whom it may concern Be it .known that I, GUSTAV R INIGKE,

4 a citizen of the German Empire, residing at Schtineberg', near Berlin, Germany, my l post-oflice address belng Heilbronnerstrasse 7, Schoneberg, near Berlin, Germany, have invented certain new and usefut Improvements in New Processes for the Production of m-Para-Alkyloxyphenylethylamins and Their N-Alkyl Derivatives, .of which the following is a specification.

and their alkyioxyphenylethylamins N- 'ja-lkyl derivatives, which products correspend to the following general formula:

Whereas X and Yisignify C I-l,,,+1 groups including hydrogen, are to be obtained in a new way and in a very simple manner as well -as in 'goodyield by transforming a primary para-alkyloxyphenylethyl alcohol of the general formula:

cm-onaon in which formula R means an alkyl group,

21,63. for instance primary 'para-methoxyphenylethyl alcohol, into the corresponding.

halid and then substituting for the halogen atom the amino .orfan 'alk'ylamino group by in'which formula X and Y mean a hydrogen atom or an alkyl group.

bromid.

Specification of Letters Patent. P t t d Jan, 30,1g12 Application filed" February 13, 1911. Serial No. 608,342,

' i My new process thus indicated represents a great progress over the prior art because these to-para-alkyloxyphenylethylamins and their N-alkyl derivatives have hitherto been obtained only by extremely detailed processes and in very poor yield.

As to the transformation of the primarypara-alkyloxypl enylethyl alcohols serving as parent material for my present invention finto thefcorresponding halids it may be eifected in any suitable manner, for instance According to mypresent-invention ro-paiaby means of a phosphorus halidx The following example may serve to illustrate my invention, the parts being by weight: 21. parts of phosphorus pentachloroform solution of the primary paramethoxyphenylethyl alcohol, which is made by mixing 15.2 parts of this alcohol with the same volume of dry chloroform. The reaction is conducted to completion on the waterbath, The product is freed from chloroform and phosphorus oxychlorid by distillation andv the' residue is heated with 30 parts'of alcoholic ammonia of about 30 per cent; strength, for some hours in a closed vessel-at about 10.0 C. The massthus produced is mixed with alkali until alkaline reaction. occurs, whereupon the volatile parts are eliminated by distillation; the residue is then'extracted with ether and the ethereal solution is'evaporated to isolate the base, which shows the known properties of the m-para-methoxyphenylethylamin. Y It is obvious to those skilled in the art that my-present invention is not limited to the foregoing example or to the details given-thereing' Thus for-instance in using in analogous manner an alkylamin instead of ammonia, for example dimethylamin, I obtain the corresponding N-alkyl derivative. It is also convenient to state that instead of the para-methoxyphenylethyl alcohol the corresponding ethoxyphenylethyl alcohol may beemployed Without departing from the scope of my'invention. Further-. more for 'thephosphorus penta-ohlorid may be substituted another sultable phosphorus halid such asfo'r instance phosphorus penta- 65 chlorid are introduced gradually into a Having now described my invention" and the manner in Whichit may be carried out the general formula:

what I ,claim is,-

1. The hereinbeforedescrihed process for the production of an w-para-alkyloxyphenylethylamin of the general formula:

in which formula R means an 'alkyl group 'Whereas X and Y signify C ll +1 groups.

including hydrogen, which process consists in acting With a suitable halogenizing agent upon a primary para-allrylozryphenylethyl alcohol of the general formula ore-omen R l I in which formula R means an alkyl group,

and treating the ire-para-alkyloiryphenylethyl halid thus obtained With an amino-base of I in which formula X 'and'Y' miean U H +l groups including hydrogen.

2. The hereinhefore-described"process for 14o iaoea the production of an wpara-alkyloxyphenylethylamin of the general formula:

l OR

in Which formula lit means an alkyl group, Whereas X and Y signify C H +1groups including hydrogen, Which process consists.

in acting'with a phosphorous halid upon a primary para-alkyloiqrphenylethyl alcohol of the general formula:

CH2CH2OH 2 in iyhich formula and Y mean C H -l-l groups including hydrogen.

In testimony whereof I have hereunto set my hand in presence oft-W0 subscribing'wit nesse's. v i

i GUSTAV REINICKE. Witnesses: HENRY HASPER,

VVQLDEMAR HAUPT. 

